Anderson achieved by age 30 what few directors have been able to do: create intelligent, quirky, independent-minded Hollywood films. Born and raised in Houston, Anderson studied philosophy at the University of Texas, where he met Owen Wilson, an aspiring actor and screenwriter. The pair collaborated on Bottle Rocket, a dark comedy about three slackers who long to be gangsters. They ran out of money shooting the feature, and trimmed it down to a short. The film caught the attention of director James L. Brooks, who helped Anderson and Wilson land a deal with Columbia Pictures to make it into a full-length film.

While the film failed to generate buzz at the box office, it did earn the team a loyal following and respectable video income. Anderson's next feature, Rushmore, starring Bill Murray and Jason Schwartzman, earned praise from critics but failed to find a wide audience. Murray earned several awards for his role as a childish millionaire who engages in a small-scale war with an ambitious teen over a prep-school teacher.

Anderson finally hit paydirt with his next outing, the idiosyncratic The Royal Tenenbaums, which starred Owen Wilson and his brother Luke. The tale of a family of precocious high achievers also featured Gwyneth Paltrow, Anjelica Huston, Gene Hackman, and Ben Stiller and earned Anderson and Wilson an Oscar nomination for Best Original Screenplay.